Amino-pyridine-containing spleen tyrosine kinase (SYK) inhibitors

A compound of the Formula (I)

• or a pharmaceutically acceptable salt thereof, wherein
• R1 is selected from the group consisting of:
• (i) —C1-C3 alkyl;
• (ii) fluoroalkyl;
• (iii) —CH2OR1a,
• wherein R1a is selected from the group consisting of H and C1-C6 alkyl;
• (iv) —N(R1b)2,
• wherein each occurrence of R1b is selected from the group consisting of H and C1-C3 alkyl, or two R1b together with the N atom to which they are attached form a group of the formula
• wherein r is 1, 2, 3, or 4;
• (v) —O—(C1-C3 alkyl);
• (vi) —N(H)C(O)—(C1-C3 alkyl);
• (vii) halo;
• (viii) H;
• and
• (ix) morpholinyl;
• R2 is —OH, —O—(C1-C3 alkyl), —N(R2a)2, —N(R2a)C(O)_R2b;
• or —F;
• wherein each occurrence of R2a is selected from the group consisting of H and C1-C3 alkyl;
• and
• R2b is C1-C6 alkyl;
• R3 is —CO2R3a, —CH2CO2R3a, —CH2CH2CO2R3a, tetrazole, —C(O)N(R3b)2, —CH2OH, H, halo, —OH C1-C6 alkyl, —O—(C1-C3 alkyl), —N(R3b)2, —CN, —C(O)N(H)S(O)2R3c, —C(O)—N(H)(R3d), —C(O)N(H)C(O)R3a, —P(O)(OR3b)2, or —B(OH)2;
• wherein R3a is selected from the group consisting of H and C1-C6 alkyl;
• wherein each R3b is independently selected from the group consisting of H and C1-C3 alkyl;
• wherein R3c is selected from the group consisting of C1-C3 alkyl, C1-C3 fluoroalkyl, C3-C6 cycloalkyl, and phenyl, wherein said phenyl is unsubstituted or substituted with one or two C1-C3 alkyl;
• wherein R3d is selected from the group consisting of —CN, —O—(C1-C3 alkyl), and tetrazole;
• R4 is —CO2R4a, —CH2CO2R4a, —CH2CH2CO2R4a, tetrazole, —C(O)N(R4b)2, —CH2OH, H, halo, —OH, C1-C6 alkyl, —O—(C1-C3 alkyl), —N(R4b)2, —CN, —C(O)N(H)S(O)2R4c, —C(O)—N(H)(R4d), —C(O)N(H)C(O)R4a, —P(O)(OR4b)2, or —B(OH)2;
• wherein R4a is selected from the group consisting of H and C1-C6 alkyl;
• wherein each R4b is independently selected from the group consisting of H and C1-C3 alkyl;
• wherein R4c is selected from the group consisting of C1-C3 alkyl, C1-C3 fluoroalkyl, C3-C6 cycloalkyl, and phenyl, wherein said phenyl is unsubstituted or substituted with one or two C1-C3 alkyl;
• wherein R4d is selected from the group consisting of —CN, —O—(C1-C3 alkyl), and tetrazole;
• R5 is —CO2R5a, —CH2CO2R5a, —CH2CH2CO2R5a, tetrazole, —C(O)N(R5b)2, —CH2OH, H, halo, —OH, C1-C6 alkyl, —O—(C1-C3 alkyl), —N(R5b)2, —CN, —C(O)N(H)S(O)2R5c, —C(O)—N(H)(R5d), —C(O)N(H)C(O)R5a, —P(O)(OR5b)2, or —B(OH)2;
• wherein R5a is selected from the group consisting of H and C1-C6 alkyl;
• wherein each R5b is independently selected from the group consisting of H and C1-C3 alkyl;
• wherein R5c is selected from the group consisting of C1-C3 alkyl, C1-C3 fluoroalkyl, C3-C6 cycloalkyl, and phenyl, wherein said phenyl is unsubstituted or substituted with one or two C1-C3 alkyl;
• wherein R5d is selected from the group consisting of —CN, —O—(C1-C3 alkyl), and tetrazole;
• R6 is selected from the group consisting of:
• (i) C1-C6 alkyl;
• (ii) C1-C3 fluoroalkyl;
• (iii) —O—(C1-C6 alkyl);
• (iv) —O—(C1-C3 fluoroalkyl);
• (v) —R6a, wherein R6a is selected from the group consisting of:
• (a) C3-C6 cycloalkyl;
• (b) a group of the formula
• wherein m is 1, 2, 3, or 4;
• (c) a group of the formula
• where R6a1 is H, C1-C3 alkyl, or —CH2CH2NH2;
• and
• (d) a 5- to 6-membered heteroaryl containing 1 to 3 heteroatoms selected from the group consisting of N, O, and S;
• wherein R6a is unsubstituted or substituted with 1 to 3 R6a2 moieties selected from the group consisting of halo and C1-C3 alkyl;
• (vi) —O—R6b,
• wherein R6b is selected from the group consisting of:
• (a) C3-C6 cycloalkyl;
• and
• (b) a group of the formula
• wherein p is 0, 1, or 2, and q is 1, 2, or 3;
• wherein R6b is unsubstituted or substituted with 1 to 2 R6b1 moieties selected from the group consisting of fluoro and C1-C3 alkyl;
• (vii) —N(R6c)2, wherein each occurrence of R6c is selected from the group consisting of H and C1-C3 alkyl;
• (viii) —N(H)C(O)—(C1-C3 alkyl);
• (ix) —N(H)C(O)O—(C1-C3 alkyl);
• (x) —NHC(O)—N(R6d)2, wherein each R6d is H or C1-C3 alkyl;
• (xi) halo;
• and
• (xii) H;
• R7 is H or halo;
• R8 is H or halo;
• R9 is H or halo;
• and
• n is 0, 1, or 2.